HCID 49855644, compound → HCID 68294157, compound

HRID 1850065Notes

Reaction equation

HRID 1850065 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[CH2:9][C:10](=[S:12])[NH2:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:14][C:15](=O)/[CH:16]=[CH:17]/[C:18]([OH:20])=[O:19]>C(O)C>[CH2:9]([C:10]1[S:12][CH:14]=[C:15](/[CH:16]=[CH:17]/[C:18]([OH:20])=[O:19])[N:11]=1)[CH:8]=[CH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 49855644HCID 49855644, compoundHCID 86702823HCID 86702823, compound

Product 1

HCID 68294157HCID 68294157, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(E)-4-phenylbut-3-enethioamide (120 mg, 0.68 mmol) was dissolved in ethanol (20 mL). (E)-5-bromo-4-oxopent-2-enoic acid (290 mg, 1.50 mmol) was then added at room temperature and the reaction mixture was stirred for 1 h. The solution was concentrated and the crude residue was purified by column chromatography to give (E)-3-(2-cinnamylthiazol-4-yl)acrylic acid (90 mg). ES+ (M+H)+ 272.

Workup

  1. concentrationThe solution was concentrated
  2. customthe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-b4fd08d41a4740558bf9d5e73ea27d5d
Source dataset
uspto-grants-2015_02
Patent number
US08957066B2

Reaction notes

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